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Place flour, sugar and salt into a bowl of food processor and process to combine. Add butter and olive oil and pulse several times to combine. Add egg yolk and pulse several more times. While pulsing, drizzle enough brandy to form a dough. Flatten, cover and refrigerate 30 minutes.
Preheat oven to 350 degrees. Place sugar in a heavy bottom pot over moderately high heat. Caramelize sugar without stirring until a light brown color is achieved. Pour caramel into the bottom of a heavy skillet or cast iron pan. Immediately place apple pieces on top mounding in center. Sprinkle with sugar and dot with butter. Roll dough to fit the pan, place on top of apples, tucking edges down around apples. Vent top with sharp knife 3-4 times and bake in hot oven 1 to 1 1/2 hours.
Remove from the oven and let stand 2 minutes. Run a sharp knife around the edge and invert onto the serving plate. Slice and serve with Michigan Apple Cream.
Whisk the cream in a large bowl until foamy. Add powdered sugar and vinegar and whisk until you can pick up and hold the cream in the whisk. Use immediately.
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